Chuck Woolery was half the pop duet "The Avant-Garde", with Elkin "Bubba" Fowler. Their one and only hit, a song called "Naturally Stoned", peaked at #40 on the charts in 1968. Elkin went on to play back-up banjo behind Leonard Cohen. Woolery released several solo singles to minimal acclaim. He was dumped by Columbia Records in 1970, subsequently signed by RCA, and dumped by RCA in 1971. In search of a career in moving pictures, he played Mr. Dingle, the toothless old mailman, on New Zoo Revue, a daily fantasy show for kids. He co-starred with Stephen Boyd and Rosey Grier in a schlocky b-grade action movie, Evil in the Deep, in 1974.

Woolery finally found his niche hosting a brief revival of Your Hit Parade in 1974, and Wheel of Fortune when it first started spinning in 1975. On Tattletales, a game show with celebrities and their spouses, Woolery often appeared with his then-wife, JoAnne Pflug. Woolery left Pflug in 1980, and left the Wheel in 1981, when he demanded a raise from $300,000 a year to $500,000. That was too much for Merv Griffin, the show's producer, and Pat Sajak took over as host of Wheel for the next few decades. Woolery's other big success was The Love Connection, a tawdry, long-running riff on The Dating Game that ran from 1981-1993. He's also hosted $1.98 Beauty Show, Scrabble, Greed, a short-lived revival of The Dating Game, Lingo, a talk show called The Chuck Woolery Show, and his own celebrity reality show, Naturally Stoned. He started his own online dating service in the late 1990s, which quickly flopped.